Conventionally, a method of a nucleophilic addition reaction to an imino group of an imine compound has been studied and, in recent years, this nucleophilic addition reaction has drawn attention as a measure for efficiently and asymmetrically synthesizing an amino acid derivative as a raw material or an intermediate for producing a pharmaceutical preparation, an agricultural chemical, a fragrance, a functional polymer or the like.
Under these circumstances, the present inventors have developed and disclosed a method for synthesizing an N-acylated amino acid derivative by a nucleophilic addition reaction to an N-acylimino ester compound by using a polymer-carrying catalyst (Journal of Combinatorial Chemistry, 2001, Vol. 3, No. 5, 401 to 403) and, further, a method for enantioselectively synthesizing these compounds by using a chiral copper catalyst (Org. Lett. Vol. 4, No. 1, 2002, 143 to 145; J. Am. Chem. Soc. Vol. 125, No. 9, 2003, 2507 to 2515).
However, the nucleophilic addition reaction on which the present inventors have studied is limited to such nucleophilic reactants as a silyl enol ether and an alkyl vinyl ether and, accordingly, a subject to which the nucleophilic addition reaction is applied and such application thereof have inevitably been restricted.
Then, under these circumstances, the present invention has an object of providing a method of an enantioselective nucleophilic addition reaction to an imine compound which enables an asymmetric synthesis of an amino acid compound or the like which is useful as a raw material or a synthesis intermediate for producing a pharmaceutical preparation, an agricultural chemical, a fragrance, a functional polymer or the like and, further, as an application thereof, a novel synthesis method of the amino acid compound or the like.